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Lookup NU author(s): Dr Jay Tromans, Dr Bian Zhang, Emeritus Professor Bernard Golding
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).
© 2024 The Royal Society of ChemistryPlasmalogens are glycerophospholipids distinguished by their O-(Z)-vinyl ether at the sn-1 position. These lipids are implicated in several disease states requiring analytical, diagnostic and therapeutic interventions, which demand synthetic availability for a variety of structural types. By deploying the new O-protecting group 1,4-dimethoxynaphthyl-2-methyl (‘DIMON’) and a new stereospecific method for accessing Z-vinyl ethers, a reproducible, versatile synthetic route to plasmalogens [plasmenyl phosphocholines] has been developed. A key intermediate is (S,Z)-1-((1,4-dimethoxynaphthalen-2-yl)methoxy)-3-(hexadec-1-en-1-yloxy)propan-2-ol, which in principle, permits plasmalogen synthesis ‘à la carte’ at scale. The methodology compares favourably with all previous synthetic routes by virtue of the very high configurational (>99% Z) and optical purity (>99% ee), including the ability to incorporate polyunsaturated fatty acyl chains (e.g. all Z docosahexaenoic acid) reliably at the sn-2 position.
Author(s): Tromans J, Zhang B, Golding BT
Publication type: Article
Publication status: Published
Journal: Organic and Biomolecular Chemistry
Year: 2024
Volume: 22
Issue: 39
Pages: 7989-7995
Online publication date: 05/09/2024
Acceptance date: 27/08/2024
Date deposited: 16/09/2024
ISSN (print): 1477-0520
ISSN (electronic): 1477-0539
Publisher: Royal Society of Chemistry
URL: https://doi.org/10.1039/D4OB01233J
DOI: 10.1039/d4ob01233j
Data Access Statement: All data reported in this paper is available on request from the corresponding author.
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